


Masochistic Angel

by ImoutoCommissions



Series: Jacob and Amy [6]
Category: Original Work
Genre: Bondage, F/M, Genital Torture, Masochism, Nipple Torture, Omorashi, Oral Sex, Piercings, Sadism, Size Difference, Spanking, Temperature Play, Urophagia, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2021-03-16
Updated: 2021-03-16
Packaged: 2021-03-25 02:54:24
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,006
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30082386
Author URL: https://archiveofourown.org/users/ImoutoCommissions/pseuds/ImoutoCommissions
Summary: Jacob spends the evening indulging Amy in her extremely masochistic desires.
Series: Jacob and Amy [6]
Series URL: https://archiveofourown.org/series/2003209
Kudos: 9





	Masochistic Angel

Amy has made it clear many times since gaining a physical form as an angel that she is a masochist. Day by day, she looks for new ways to push those limits, and indulge herself in her love for pain, and Jacob is always willing to go along with that. It makes it a lot easier for him to not have to worry about her, knowing that she can heal anything, no matter what may happen to her, so even if she gets the urge to take things “too far,” she is always just fine. That being said, he is starting to think that there is no such thing as too far for his little angel.

Today, she is naked in one of the spare rooms in this house that would be much too big for him living on his own. She has golden cuffs on her wrists, with thick chains suspending her from the ceiling, and she has leather bands on her wings, preventing flight and levitation. There is just enough slack in the chains for her feet to touch the floor, but only if she stands perfectly straight while she does so.

Amy has no way of telling the time, so she does not know how long she has been restrained like this. All she knows is that Jacob made her skip her morning pee and drink a lot at breakfast, promising her something fun when he got home from work. Since then, she has just been left to cope with her bladder filling rapidly, and for some time now, it has been absolutely bursting, with Amy unable to keep still, squirming in her chains, doing everything that she can to take her mind off of it, while trying to keep her weight off her wrists when she wriggles around.

The only distraction that she has throughout the day are her babies gliding in to visit her for lunch, and beyond that, she is on her own, bouncing from foot to foot, and hoping that her bladder does not give in before he gets home. All the while, she is caught up in anticipation, wondering what he has in mind for her when he returns, since he was so vague about it all. It could be anything, but she has a feeling it will not be nearly as fun as he has promised if she is not able to hold it until he gets back.

But she feels as if she might go crazy from both the desperation and the anticipation, and right when she is certain that she is at the edge of her sanity, she hears Jacob enter the house, and start making his way up to see her. Amy is writhing by the time he enters the room and says, “Hello, I’m home! How’s my little angel doing?” First, he pats her on the head, which she rather likes, but then, he presses a hand against her bladder bulge, rock hard with how full she is.

Whining, Amy cries, “Please, you’re going to make my piddle pot pop!”

Jacob chuckles at her reaction and says, “Well, I have a lot in store for you this evening! For one thing, I managed to find some fertility drugs for you, since you’re so eager to have bunches of angel babies!” With that, he pinches her nose to tip her head back, so that he can toss a few pills in her mouth, before forcing her to wash them down with a whole litre of water.

Amy no longer needs to breathe, but she still splutters when he lets go of her, being a bit dramatic. At the same time, Jacob brandishes a fly swatter at her, saying, “I’m going to have to use this to punish you!”

“No, not that!” she wails, doing her best to put on a terrified expression, but it is far too easy to tell that the little masochist is excited by the prospect. He circles behind her with it, brushing it along one of her cheeks, before pulling it back and bringing it down, smack onto her rear. As it strikes her, she lets out a loud yelp.

Jacob begins alternating between her left and right cheeks, swatting her on both, while Amy, between her yelps of pain, encourages him and lists off things that she has done that he can discipline her for, though he knows for a fact that some of them are made up in the heat of the moment. “I’m a naughty little angel, because I make messes in the kitchen when I cook, and I try to make babies with you, and I break things on purpose, and I cause all kinds of trouble! I’m addicted to my new big brother’s thingie and I’m really, really bad!”

She doesn’t really need to make up things, or even list the things that she has actually done, to get Jacob to keep punishing her, but he appreciates her efforts, finding it adorable the lengths she will go to in order to make sure that she is punished to her heart’s content, always begging him for more, always so eager to have him punish her over and over again. He takes her time to make sure that her rear is thoroughly reddened, and then begins to make on, taking his punishment to other places, swatting up and down the backs of her thighs, while Amy starts to list the things she did as a ghost.

“I spied on lots of grown ups to try and learn what they were doing, and then when my big brother moved in, I tried to learn how to do those things with him, and I would sneak all around, and…and…” The things that she says become less coherent, all as she tries to make sense of what to say, and while she indulges more in the feeling of pain, running out of things to get herself in trouble, with Jacob still never slowing his punishment.

He soon switches to swatting her flat chest, as well as her trim tummy, moving up and down as he punishes her, down to the front of her thighs and then back up, as she struggles to think of things to say, blurting out anything that comes to mind, just to keep him swatting her. Soon enough, he has directed the brunt of his strikes to her bursting bladder, making sure that he puts extra force into those.

Crisscrossing swatter marks all over her, he pushes the swatter between her legs and says, “Spread them.” She ends up on her tiptoes with her legs spread, where he can see her glistening girlhood, able to see just how wet she is from her arousal. With that, he brings the swatter up between them, and when she cries out, it is halfway from pain, and halfway from pleasure, and it leaves her moaning for more.

“Please, swat my naughty twatty some more!” she begs him. He does exactly that, and moves around the rest of her body as well, making sure that he does not miss anything, giving her all of the physical punishment that his masochistic angel desires from him. He spends several minutes swatting her like this, until finally, she is left hanging limply in her chains, doing her best to catch her breath, while Jacob goes to get something else that he brought for her surprise.

“Now, here’s what we’re going to do next,” he says, as he holds up a needle, with a whole package of them. Her eyes widen when she sees it- it is a thick needle, meant to be used with yarn, and very sharp, so that it can penetrate the thickest of fabric. And as he moves back over to her and takes one of her nipples between his thumb and forefinger, rolling it between his fingertips, he makes it rather clear what he plans to do with them, all without having to say a single word.

“No, no, not that! Don’t do that!” she cries, her voice distressed as she begs him, but she is squirming in excitement, and her facial expression does not match her tone of voice. No matter how hard she tries to act like she hates such things, she is never that good of an actress, and always gives away her excitement either way, her masochism on full display.

She continues to beg him to stop, to wait, while her body gives off the opposite message, as Jacob manages to force a needle through her nipple, causing her to let out a sharp scream of pain. However, there is no blood resulting from the wound, and he withdraws his hands, so that he can get another needle from the package. Amy is too dazed now to keep up begging him to stop, but she is soon screaming again, as he does the exact some to her other nipple, both pierced horizontally by the pair of needles.

Like this, he is able to hook his middle finger and index finger around either side of both needles, and then, when he twists it, he twists her nipple as well, and Amy screams out, eyes rolling back in her head. Now, she is not even trying to pretend that she does not want it, and between her screams of pain, she moans out encouragement, begging him to continue the abuse.

“Twist them, twist them!” she begs. “Harder, do it harder! Hurt my nippies, twist them hard, twist them so hard that they pop right off!” He does not quite give into her more extreme demands, but he does keep it up for a bit, just to indulge her, before giving her a chance to recover.

However, while he lets her nipple piercings recover, he gets down in front of her to pinch at her clit, making his new intentions very clear to her. Taking a third needle, he menacingly points the tip toward her clit, and Amy tries to keep up her act of not being very much into the torture that he inflicts on her, and she moans out, “No, no, don’t stick that needle in my bud! Please, don’t stick it in there, whatever you do!”

Naturally, he ignores her pleas, and she does not really mean it anyway, and as he forces it into her clit, pushing it deep as she lets out an ear piercing scream of both pain and pleasure, sent into the convulsions of an intense, gushing orgasm that leaves her writhing after, multiple orgasms wracking her form as the pain does not end, with Jacob twisting the needly by the eyelet, digging it into her clit in order to sustain this feeling. Jacob keeps this up until he decides that she has had enough, wanting to give her another chance to recover.

By the time she has had a chance to rest up from all of that, the swatter marks have begun to heal up, leaving her rear completely unblemished, as if it never happened at all. For the next level of torture, he goes down to the kitchen, returning with potato mashers that have been heating up in boiling water, so hot that the first time he presses one of them to her buttcheek, she lets out a sharp cry as it sears into her flesh. When Jacob pulls it back, there is a waffle pattern left behind.

He is quick to use a second masher on the other cheek, so that he can burn it in much the same way, and Amy is left writhing from the painful pleasure of having her skin burned. Jacob gives an open palmed slap to each before commenting, “They’re almost like little waffle looking cutie marks from that show you like to watch, aren’t they?”

With that fun out of the way, it is time to turn his attention to the most important matter of the evening, what she has been waiting for all day. “Show me your bladder and your kidneys,” he orders her, and skin turns transparent, letting him see the organs he desires. “And make sure I can touch your bladder as well.” As soon as he has added that, he reaches forward, his hand able to pass through into her so easily, allowing him to grab hold of her bladder and make her wince at the contact. Like this, it is easy for him to play with it like an overfilled water balloon, squeezing it in his hand, feeling how the liquid inside is just straining to get free, why Amy whimpers and whines, squirming uncontrollably as she tries to fight off the desperate urge to let it all go right now- though neither are sure if she would be able to with the way he is handling her.

As he holds her bladder steady, he gets a third potato masher, but this one was not held in boiling water- instead, it had sat in ice water, so when he presses it right against her bladder, she is overwhelmed by the cold of it all, no doubt increasing her desperation. However, as Amy is left shivering, she voices a genuine complain, rather than her usual act of not enjoying something.

“I don’t like that,” she whines. “I hate being cold, you know that…cold feelings just remind me of…remind me of…” She trails off, but there is no need for her to finish her sentence for Jacob to understand what she is trying to say. For half a century, she was left in perpetual cold due to her ghostly form, stuck feeling the same freeze she felt the winter night that she died, and the only warmth that could ever be found was in his embrace.

He probably should have thought about that before, but he was just excited to see if she was into temperature play and how it would effect her desperation. “I’m very sorry, I didn’t consider that and I should have,” he says sincerely, hoping that his thoughtlessness will not ruin the fun that they have had so far, and that he has planned for her.

“I forgive you,” she says, “but you’d better keep going and give me lots more fun to make sure that I don’t get mad all over again!” He is relieved to see that she is just as enthusiastic as ever before. Now, he cuffs her ankles, and attaches those cuffs to chains that attach her to the ceiling as well, while allowing the chains on her arms a little more slack, moving her so that she is hovering and reclining, face and pelvis both at waist level with Jacob.

He goes to stand behind her, so that he can take advantage of this position by making her tilt her head back. This way, he can push his cock past her lips and start fucking that cute mouth of hers, her jaw barely able to handle just how much his girth has been enhanced due to their repeated fucking, and her angelic abilities. But since she does not need to breathe, he also does not need to worry about going easy on her as he forces it all the way into her mouth, forcing it all the way down her throat, while she makes exaggerated gagging sounds, all as a part of keeping up with the illusion of being tortured.

It is not long before he has begun roughly thrusting down her throat, moaning as he takes full advantage of this position, using her to his heart’s content to get himself off. After he has had this going for a little while, he reaches his hands down to grab hold of her nipple piercings, twisting the needles again for another round of torture, so that he can make her throat vibrate around his cock as she attempts to scream out in agony, giving him delighted shudders of pleasure.

The harder he twists, the more she moans and screams around him, the sound getting trapped in her throat, and he watches her go to absolute pieces just like this, indulging in this for a while before he speaks up to say, “Show me your stomach.”

She does as she is told, just in time for him to give into his pleasure and unleash a massive load, enough to take her stomach from completely empty to full enough to have a stomach ache, flooding her with his seed, and even as he starts to pull out, she is left sputtering and spitting it up, and there is still a little bit left to splatter her face. The more they do this, the more intense his orgasms become, and he gives her so much that she can hardly handle it, but that’s exactly what she wants.

Now, he moves between her legs, so that he can wiggle the needle in her clit a little more, causing her to writhe in the pain and pleasure, before he suddenly yanks it right out. Before Amy can recover from any of this, he has thrust forward, slamming inside of her pussy and popping her cherry all in one go. Once he is buried inside of her, she is left screaming, unable to think or speak, with Jacob so big that he would challenge anyone, let alone a tiny angel who heals back to the state of virginity every time that he is done with her.

But she loves it all so much, loves every second that she gets to spend in pain because of him. He is still not sure how she turned into such a little masochist, even after the novelty of pain wore off, but he also can’t fathom not being able to feel much of anything for as long as she did, so it is more than he can wrap his head around. Besides, she may have always been destined to turn out this much of a slut for pain, no matter where her life had taken her.

He begins fucking her pussy even harder than he fucked her face, and Amy is left screaming out her encouragements for him, barely able to find her voice, but still finding a way to keep begging him for more. At first, she starts with crying out things like, “Yes, fill my kitty with your cream!” but quickly escalates to full on vulgarity, saying words that she once would have considered too dirty to ever let past her lips, but he has managed to corrupt not only a little girl, but an angel, at that.

“Fuck me! Fuck me harder, give me lots more babies!” she whines for him, and Jacob is more than eager to comply, and give her everything that she wants. That is why he does not slow down, knowing that the rough way he fucks her is all she needs to get off, needing only pain for her pleasure, and wanting him to focus on getting himself off more than anything else, so that he will be able to fill her right up, and surely knock her up like she wants.

“Knock me up!” she begs him. “Give me so many babies my angel belly gets too big for me to move!” As she speaks, she exposes her womb and her ovaries to him, not even needing him to tell her to do that, because she wants so badly for him to play with her like that. Jacob reaches through to comply, gently fondling her ovaries in his hands, a sharp contrast to the rough way that he is fucking her, and she gasps and moans from the added stimulation, until she is soon begging, “Squish my squishies!”

“Now, I can’t do that,” he replies, his voice even and reasonable despite the strain all of this is putting on him. “That’s where your eggs come from, so if I did that, I wouldn’t be able to put any angel babies in your belly tonight.” As he says that, he does give her a light squeeze, not enough to really hurt her, but at least something like what she wants, before pulling them so that her “stringies” are pulled taut, where he is then able to pluck at them like guitar strings, making her eyes roll back in her head as she cries out.

Teasing her like this is fun, but there is not much more he can do before he completely loses himself. She is so perfectly tight around him, and he can see just how big he is, how he is much too big for her, and he is unable to hold back as he gives into his pleasure, exploding inside of her with his climax. With another massive load pumped into her, she is quickly filled and overfilled by his seed, her womb expanding so much to try and fit it all, with a little bit already leaking out around his cock. Jacob is left panting as he tries to recover from this climax, hoping that that was enough to knock her up, but certain that they are going to achieve it soon either way.

Just to be on the safe side, he is careful as he pulls out to make sure that she does not leak too much, and undoes the cuffs around her wrists, shortening the slack on her ankle chains, until she is dangling upside down, forced into a handstand, all to make sure that she does not leak any of his come out of her bloated womb, swollen about as much as her bursting bladder is by now.

With that in mind, he remembers that he needs to check on that. First, however, he goes to get the needle, working it back into her clit, her dazed whimpers quickly turning to screams as she revels in the fresh burst of pain that it causes, having nearly already healed up from having it removed. Once he has that secured in place, driven deep into her clit, he gets a vibrator, turning it up as he works it into her pussy, still so tight, probably already returned to a virginal state, so that he leaves his little angel writhing and moaning in pleasure.

Finally, he puts a hand to her bladder to feel just how much she is holding right now, stunned by just how hard it feels, and how swollen it has become. He had checked when he first got home, but it is clear that the water he made her drink when she took her pills has hit her now, and is making it that much worse for her. He knows that Amy is not going to be able to hold it for much longer, and that makes him want to torture her that much more, and see what she can handle.

He reaches down to pluck a feather from either of her wings, still bound so that she is unable to use them, and she winces a bit at the sudden, pinching pain, though it is hardly anything compared to the pain that she has endured already during this session. What he has in mind now is not the painful sort of torture, though; however, it will definitely cause her some level of pain, as it puts additional strain on her bladder, already stressed so much that it is a wonder that she is able to hold back at all.

On either side of her, he is able to use the feathers to tickle her, starting at her hips and working his way down, as she begins squirming and thrashing in her bonds, squealing with laughter, so breathless that she can’t properly protest, though he knows that is not for lack of trying. It is adorable, watching her struggle like this, laughing too hard to express how much it hurts her to be tickled like this in her current state, and beneath all of that pain and protest, there is still pleasure, because she loves that pain more than anything.

Jacob keeps up the tickle torture for a while, just to keep her screaming for him, howling with laughter while she tries to warn him about her impending accident. Even though she is not able to properly get it out, he knows exactly what it is that she is trying to say, but she manages to surprise both of them by keeping it all in, not even leaking, despite how strong the temptation may be, and despite how her bladder must be absolutely straining right now, wanting so badly to empty out.

The fact that she can handle herself so well is proof of how much practice she has had at this, and since she does not need to breathe, he does not have to worry about her getting too out of breath from all of her gasping laughter. Finally, though, he does slow to a stop, letting her giggle as she tries to recover from all of the tickling, still writhing in her desperation, and still trying to find the words to speak to him.

“You almost made me pee!” she finally whines, once she regains her voice. “You know I’m about to burst, you made me hold it all day!”

“I know, I know,” he says, putting on a fake voice of sympathy. He knows exactly what he has done, and she knows just as well as he does that he does not actually feel any remorse for that. Even so, he acts as if he is showing her mercy as he says, “Well, don’t worry, I’m going to let you empty your bladder now. You did a good job holding it for me all day, just like I asked you to, so there’s no need for me to make you keep waiting.”

Amy seems as if she is waiting for him to get her down, but instead, he goes to get yet another device he prepared for this occasion. As soon as she sees the catheter, she knows that things are not what she is expecting, but she is stunned when she realizes that it is connected to a long tube that ends in a mouth piece. Jacob secures that piece along her mouth, and once she is all set up, there is nothing she can do to stop him from using a pump to empty her bladder, her urine flowing into the tube, and going straight into her mouth.

Of course, she finds the taste of her own urine just as nice and Jacob always has, but there certainly is a lot of it for her to drink down, and with the way things are currently set up, she has no choice but to finish it all, swallowing it all down. She has been holding a lot all day, and even though it feels absolutely amazing to finally be able to empty her overfull bladder, she knows that it is not accomplishing much, because every bit that she drinks down is going to have to come back out soon enough.

And so, she can’t help but shiver in anticipation, thinking about how quickly this is all going to find its way back to her bladder, and how soon she is going to be desperate all over again. She has a feeling that even then, James is not going to make things easy for her, and of course, she looks forward to seeing what happens at that time. For now, though, she can at least enjoy the bliss of finally being able to empty out, swallowing down the last of her stored up pee.

Once she is done drinking that, Jacob finally lets her down, completely freeing her from the bonds that she has been trapped in all day. He scoops her up, carrying her bridal style as he says, “After all that excitement, I think a bath is in order.”

Normally, the two might get up to all kinds of trouble, sharing a bath together, today is an exception to that, with both having had plenty of excitement to last the day. Instead, they simply enjoy their time in the bath, with Amy finally getting to relax as her big brother helps her get cleaned up. After that, the babies enjoy their dinner, drinking from Amy’s breasts, and Amy and Jacob order pizza to satisfy their own hunger, since both are far too worn out to even think about cooking anything.

Not long after they have finished eating, when it is getting close to time for the two of them to start getting ready for bed, all that she has had to drink hits her bladder- again. Her desperation returns with a vengeance, hitting her all at once and making her wince with the intensity of it all, her sudden need to pee severe.

Immediately, she breaks out into a full potty dance, hands jammed between her legs as she squirms and hops from foot to foot, making her predicament clear to Jacob at a glance. She has just been dressed in a nightie to get ready for bed, and Jacob intends to go to bed just like they planned, ignoring the way she starts whining about how she needs to go right away.

“It’s time for bed, so you’re not allowed to go anywhere near the toilet until morning,” he tells her, scooping her up so that he can take her to bed.

“But I’m going to wet the bed!” she whines, knowing that must be true. She already feels like she could wet herself at any moment, so how can he expect her to hold it all night long? Her bladder may be able to take a lot, but she is sure that there is no way she can last that long.

Jacob seems to think otherwise, and tells her, “If you wake up with piddly panties, then I’m not going to give you your morning creampie.”

“But that’s not fair!” Amy protests, though now she has a greater incentive to try and do the impossible.

**Author's Note:**

> If you're interested in my writing updates, please follow my fanfiction twitter @WattStalf


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